As Pittsburgh strives to revive its image as a river city it must contend with its dilapidated urban riverfronts along the Monongahela, Allegheny, and Ohio Rivers. In the late 19th and 20th centuries, the river was considered solely as an economic engine that fueled the growth of America. Once the world’s largest producer of glass and steel, Pittsburgh’s popular South Side district has become disconnected from the river, despite its close proximity. The purpose of this thesis is to generate a new vision plan for the South Side by reprogramming the neglected margin with the intention of providing public access and activating the life-less boundary between the community and the riverfront. In response to the inadequacies of some recent projects completed within the city, this project suggests a new model for the South Side that aims to integrate the riverfront with the urban fabric. The process focuses on the neglected riverfront by extending programs from the surrounding context to pollinate the marginal spaces. An exploratory method is developed to create an open space framework that is capable of supporting the diverse social and cultural demands of Pittsburgh’s South Side. It demonstrates that strategic urban design can effectively create new viable connections with the river by creating spaces that are flexible enough to facilitate the changing demands on the urban riverfront.